EP2814917B1 - Additifs ameliorant la resistance a l'usure et au lacquering de carburants de type gazole ou biogazole - Google Patents

Additifs ameliorant la resistance a l'usure et au lacquering de carburants de type gazole ou biogazole Download PDF

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Publication number
EP2814917B1
EP2814917B1 EP13704128.1A EP13704128A EP2814917B1 EP 2814917 B1 EP2814917 B1 EP 2814917B1 EP 13704128 A EP13704128 A EP 13704128A EP 2814917 B1 EP2814917 B1 EP 2814917B1
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Prior art keywords
additives
diesel
ppm
les
diglycerol
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German (de)
English (en)
French (fr)
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EP2814917A1 (fr
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Mathieu ARONDEL
Thomas Dubois
Laurent Germanaud
Hélène Rodeschini
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TotalEnergies Marketing Services SA
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Total Marketing Services SA
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Definitions

  • the present invention relates to the use of additives to improve the resistance to lacquering of fuels of the (bio) diesel type of superior quality.
  • the processes for preparing low-sulfur diesel or diesel fuel bases for example hydrotreatment processes, in addition to reducing the sulfur content, also reduce the content of these diesel fuel bases in polycyclic aromatic compounds and in polar compounds.
  • diesel fuels or diesel with low (less than 100 ppmm) or even very low sulfur content have a reduced ability to lubricate the injection system of the engine, which means that for example the injection pump of engine fuel may fail early in the life of the engine, such as failure in high pressure fuel injection systems, such as high pressure rotary distributors, in-line pumps , combined pumps, with injectors and injectors.
  • Lubricants and / or antiwear additives for fuel oils have been described in EP 680 506 ; these additives include an ester of a carboxylic acid and an alcohol, in which the acid has from 2 to 50 carbon atoms, and the alcohol has one or more atoms; one of the preferred additives is glycerol monooleate (GMO).
  • GMO glycerol monooleate
  • EP 915,944 are described anti-wear additives for diesel fuels with low sulfur content constituted by a combination of at least one aliphatic monocarboxylic hydrocarbon, saturated or unsaturated, of linear chain between 12 and 24 carbon atoms and at least one hydrocarbon compound polycyclic chosen from the group consisting of natural resin acids, and carboxylate derivatives of amines, esters and nitriles of these acids.
  • These additives can for example be derived from tall oil (in English "tall oil”).
  • additives are described to improve the resistance to lacquering of diesel fuels.
  • Diesel fuels sold must comply with national or supranational specifications (for example the EN 590 standard for diesel fuels in the EU).
  • additives chemical compounds incorporated into fuels to improve their properties, for example additives improving cold resistance
  • oil companies, distributors are free to add or not additives to their fuels.
  • first price fuels
  • higher quality fuels in which one or more additives are incorporated to improve their performance (beyond regulatory performance).
  • high quality fuel of the diesel or biodiesel type means any diesel fuel or biodiesel additive with at least 50 ppm by mass of at least one compound chosen from deposit reducers, detergents, dispersants.
  • diesel fuels of type B0 which do not contain an oxygenated compound
  • biodiesel fuels of type Bx which contain x% (v / v) of vegetable oil esters or fatty acids, most often methyl esters.
  • EMHV or EMAG EMG
  • lacquering This deposit phenomenon is also known under the English term lacquering which will be used in the description which follows or under the English acronym IDID (internai diesel injector deposits).
  • IDID internal diesel injector deposits
  • the phenomenon of lacquering does not relate to deposits external to the injection system relating to coking (coking in English) or clogging of injection nozzles (nozzle coking or fouling) as simulated for example by the standard engine test CEC F098-08 DW10B, in particular when the fuel tested is contaminated with metallic zinc.
  • the lacquering phenomenon can be localized on the end of the injector needles, both on the head and on the body of the needles of the fuel injection system but also in the whole control system of the lifting of needles (valves) of the injection system, for the engines of vehicles running on diesel or biodiesel fuel, and in particular for higher quality (bio) diesel fuels.
  • This lacquering phenomenon can ultimately generate a loss of flow of injected fuel and therefore a loss of engine power.
  • esters obtained from carboxylic acids comprising from 11 to 21 carbon atoms and from diglycerol, oligoglycerols and / or polyglycerols. These esters are used to improve the lubricity of diesel fuel. This document does not concern the improvement of the resistance to lacquering of fuels of the (bio) diesel type of superior quality.
  • the deposits due to the lacquering phenomenon are insoluble in low sulfur diesel fuels and biodiesel fuels. These deposits exist in the form of fine particles and can pass through diesel filters and settle inside the injectors.
  • the present invention overcomes the drawbacks indicated above.
  • the present invention provides additives capable of tangibly improving not only the wear resistance of (bio) diesel or bio (diesel) fuels with low sulfur content, typically less than 100 ppm by mass, but also the resistance to lacquering.
  • high quality (bio) diesel fuels ie additives with at least 50 ppm by mass of at least one compound chosen from deposit reducers, detergents, dispersants.
  • the present invention relates to the use of additives to improve the lacquering resistance of fuels of the (bio) diesel type of superior quality, said additives comprising at least 50% by mass of monoester (s) and / or diester (s) of polyglycerols, said polyglycerols having from 2 to 5 glycerol units per molecule and the ester units being derived from fatty acid (s), the fatty acid or acids optionally having one or more ethylenic unsaturations, and more than 50% by number of fatty chains comprising between 12 and 24 carbon atoms.
  • additives comprising at least 50% by mass of monoester (s) and / or diester (s) of polyglycerols, said polyglycerols having from 2 to 5 glycerol units per molecule and the ester units being derived from fatty acid (s), the fatty acid or acids optionally having one or more ethylenic unsaturations, and more than 50% by number of fatty chains comprising between 12 and 24
  • the term “superior quality fuel of the diesel or biodiesel type” means any diesel or biodiesel fuel, in which one or more additives are incorporated to improve its performance (beyond regulatory performance), preferably, any diesel fuel or biodiesel additive with at least 50 ppm by mass of minus one compound chosen from deposit reducers, detergents, dispersants.
  • the deposit reducer / detergent / dispersant is chosen from: ⁇ substituted succinic acid anhydrides, in particular polyisobutenyl succinic anhydrides, often called PIBSA, in which the polyisobutylene group (also called polyisobutene) has a molecular mass of between 140 and 5000 and preferably between 500 and 2000 or preferably between 750 and 1250,
  • Another subject of the invention relates to (bio) diesel fuels of superior quality and of improved lacquering resistance, additives with at least 50 ppm m / m of at least one compound chosen from deposit reducers, detergents, dispersants and with at least one additive as defined in the present invention.
  • glycerol into polyglycerols (PG) and into polyglycerol esters (EPG) is an important reaction leading, as indicated above, to various biodegradable surfactants very widely used in industry.
  • Polyglycerols can be obtained by oligomerization of glycerol. Generally, the reaction is carried out in the presence of homogeneous or heterogeneous acidic or basic catalysts.
  • polyglycerols are mixtures of close homologues with a majority targeted molecule.
  • diglycerol marketed by the company Fluka has the following distribution with 87% diglycerol and 10% tri- and tetraglycerol.
  • mono- and diesters of fatty acid (s) and polyglycerol (s) are known per se; they can for example be prepared by esterification of fatty acid (s) and of diglycerol in the case of the mono- and diesters of diglycerol (or of triglycerol in the case of the mono- and diesters of triglycerol).
  • the product resulting from this esterification reaction comprises a mixture of mono-, di-; polyglycerol tri- and tetra-esters (for example diglycerol, triglycerol, mixture of di- and triglycerol), as well as small amounts of fatty acid (s) and polyglycerol, (for example diglycerol, triglycerol, mixture of di- and triglycerol) which have not reacted.
  • the patent EP 1,679,300 describes a process for producing fatty acid esters and polyglycerol, in which glycerol is added to a reaction mixture obtained by a direct esterification reaction between polyglycerol and a fatty acid at a temperature ranging from 60 ° C to below 180 ° C, and the glycerol phase containing unreacted polyglycerols is separated and removed.
  • Esters of fatty acid (s) and polyglycerols have long been known as nonionic surfactants; being biodegradable and biocompatible, they are used in particular for food and personal care.
  • polyglycerol esters are described as “Fuel Economy” additives for any type of fuel; only decaglycerol tetraoleate is exemplified in a petrol fuel as a “Fuel Economy” additive.
  • Polyglycerols can be represented by one of the following general formulas: where n ⁇ 2, represents the number of glycerol units of the polyglycerol.
  • Polyglycerols are characterized by their molecular mass, their number of hydroxyl groups and their hydroxyl number, as mentioned in the table below.
  • polyglycerol not Molecular weight Number of OH Hydroxyl number (mg KOH / g) diglycerol 2 166 4 1352 triglycerol 3 240 5 1169 tetraglycerol 4 314 6 1071 pentaglycerol 5 388 7 1012
  • the fatty acids from which the polyglycerol esters according to the invention are derived can be chosen from stearate, isostearate, oleate, linoleate, linolenate, behenate, arachidonate, ricinoleate, palmitate, myristate, laurate, caprate, and their mixtures and the corresponding esters such as the Diglyceryl monostearate mixture ( CAS 12694-22-3 ), Polyglyceryl - 2 diisostearate, or diglyceryl diisostearate ( CAS 67938-21-0 ), Polyglyceryl-2 isostearate ( CAS 73296-86-3 ), Polyglyceryl-2 isostearate ( CAS 81752-33-2 ), Polyglyceryl-2 oleate ( CAS 96499-68-2 ), Diglyceryl monooleate ( CAS 49553-76-6 ), Polyglyceryl-2 triisostearate ( CAS 120486-24-0 ), 3-pol
  • the fatty acids can come from the transesterification or saponification of vegetable oils and / or animal fats.
  • the preferred vegetable oils and / or animal fats will be chosen as a function of their oleic acid concentration. We can refer for example to Table 6.21 of chapter 6 of the book Carburants & Moteurs by JC Guibet and E. Faure, 2007 edition in which the compositions of several vegetable oils and animal fats are indicated.
  • the fatty acids may also come from fatty acids derived from tall oil (in English "tall oil fatty acid” TOFA) which comprise a majority amount of fatty acids, typically greater than or equal to 90% by mass as well as resin acids and unsaponifiable in a minority quantity, ie in quantities generally less than 10% by mass.
  • tall oil in English "tall oil fatty acid” TOFA
  • Preferred additives according to the invention capable of improving the wear resistance of low sulfur (bio) diesel fuels and the lacquering resistance of high quality (bio) diesel fuels include partial esters of diglycerol or triglycerol with at least 50% by mass of monoester - and / or diester (s) of oleic acid and diglycerol, therefore of mono-oleate (s) of diglycerol (DGMO) and / or dioleate (s) of diglycerol (DGDO).
  • additives comprise at least 50% by mass of mono-and / or diester (s) of oleic acid and of triglycerol, therefore of mono-oleate (s) of triglycerol and / or of dioleate (s) of triglycerol.
  • additives comprise at least 50% by mass of mono-and / or diester (s) of oleic acid and diglycerol and / or triglycerol.
  • Diesel fuels liquid fuels for compression engines
  • middle distillates with a boiling temperature between 100 and 500 ° C; their starting crystallization temperature TCC is often greater than or equal to -20 ° C, generally between -15 ° C and + 10 ° C.
  • These distillates are mixtures of bases which can be chosen, for example, from distillates obtained by direct distillation of petroleum or crude hydrocarbons, vacuum distillates, hydrotreated distillates, distillates from catalytic cracking and / or hydrocracking of vacuum distillates, distillates resulting from ARDS conversion processes ( by atmospheric residue desulfurization) and / or visbreaking.
  • Diesel fuels can also contain light cuts such as petrol obtained from distillation, catalytic or thermal cracking units, isomerization, desulphurization alkylation units, steam cracking units.
  • These new fuel and combustible bases can be used alone or in mixture with conventional petroleum middle distillates as fuel base (s); they generally comprise long paraffinic chains greater than or equal to 10 carbon atoms and preferably from C14 to C30.
  • diesel fuels have a sulfur content less than or equal to 500 ppm by mass, advantageously less than or equal to 100 ppm by mass, and which can be lowered to a content less than or equal to 50 ppm by mass, or even even less than or equal to 10 ppm by mass (this is the case of diesel fuels for current vehicles whose sulfur level according to the European standard EN 590 currently in force must be less than or equal to 10 ppm by mass).
  • the wear resistance and lacquering resistance additives for diesel fuels according to the invention can be incorporated into fuels up to a value of up to 10% by mass, and advantageously so that the concentration of mono- and diglycerol and / or triglycerol di-ester (s) in the final fuel is between 20 and 1,000 ppm by mass, and preferably between 30 and 200 ppm by mass m / m, that is to say ppm by mass based on the total mass of the additive fuel.
  • the top quality (bio) diesel fuel compositions contain at least 50 ppm by mass of at least one compound chosen from deposit reducers, detergents, dispersants and contain at least one additive according to the invention. invention and optionally at least one or more other functional additives.
  • the anti-wear and anti-lacquering additives of the present invention can be used alone or in admixture with other functional additives, such as deposit reducers / dispersants, antioxidants, combustion improvers, corrosion inhibitors , cold-keeping additives (improving cloud point, sedimentation rate, filterability and / or cold flow), dyes, demulsifiers, metal deactivators, defoamers, agents improving the cetane number, co-solvents, compatibilizing agents, other anti-wear additives than those of the present invention, etc.
  • functional additives such as deposit reducers / dispersants, antioxidants, combustion improvers, corrosion inhibitors , cold-keeping additives (improving cloud point, sedimentation rate, filterability and / or cold flow), dyes, demulsifiers, metal deactivators, defoamers, agents improving the cetane number, co-solvents, compatibilizing agents, other anti-wear additives than those of the present invention, etc.
  • any other additives are generally incorporated in amounts ranging from 50 to 1,500 ppm m / m, that is to say ppm by mass based on the total mass of the additive fuel.
  • additives can be incorporated into fuels according to any known process; by way of example, the additive or the mixture of additives can be incorporated in the form of a concentrate comprising the additive (s) and a solvent, compatible with the (bio) diesel fuel, the additive being dispersed or dissolved in the solvent.
  • a concentrate comprising the additive (s) and a solvent, compatible with the (bio) diesel fuel, the additive being dispersed or dissolved in the solvent.
  • Such concentrates generally contain from 20 to 95% by mass of solvents.
  • Solvents are organic solvents which generally contain hydrocarbon solvents.
  • solvents such as petroleum fractions, such as naphtha, kerosene, heating oil; aliphatic and / or aromatic aromatic hydrocarbons such as hexane, pentane, decane, pentadecane, toluene, xylene, and / or ethylbenzene and alkoxyalkanols such as 2-butoxyethanol and / or mixtures of hydrocarbons such as mixtures of commercial solvents such as Solvarex 10, Solvarex LN, Solvent Naphta, Shellsol AB, Shellsol D, Solvesso 150, Solvesso 150 ND, Solvesso 200, Exxsol, ISOPAR and possibly polar dissolution aids, such as 2-ethylhexanol, decanol, isodecanol and / or isotridecanol.
  • the invention relates to the use of at least one composition of additives according to the invention incorporated in a diesel or biodiesel fuel of superior quality to improve resistance to lacquering, ie fouling on the head and / or on the body. of the needles of the fuel injection system but also throughout the system for controlling the lifting of needles (valves) of the injection system, in particular for engines fitted with fuel injection systems of Euro 4 to Euro 6 type.
  • the invention also relates to a method for improving lacquering resistance comprising the introduction of additives into a fuel of high quality (bio) diesel type, said additives comprising at least 50% by mass of monoester (s) and / or diester (s) of polyglycerols, said polyglycerols having from 2 to 5 glycerol units per molecule is the ester units being derived from fatty acid (s), the fatty acid (s) optionally having one or more ethylenic unsaturations, and more than 50% by number of fatty chains comprising between 12 and 24 carbon atoms.
  • the method of improving the lacquering resistance according to the invention also makes it possible to improve the resistance to wear, in particular of injectors, and the lubricity of (bio) diesel fuels having a rate of sulfur less than or equal to 500 ppm by mass.
  • the technology used for the injectors requires a high fuel return, which promotes the degradation of the fuel since it can be subjected to several cycles in the high pressure pump and the Common Ball before being injected into the combustion chamber.
  • the characteristic temperatures of the various fluids allow the validity of the tests to be checked.
  • the fuel is regulated at 65 ° C at the pump inlet
  • the coolant is regulated at 90 ° C at the engine outlet.
  • the smoke values make it possible to control the timing of combustion at the start of the test (target value of 3FSN) and to ensure that it is well repeatable from one test to another.
  • Table 1 The mass composition of the products obtained, measured by steric exclusion chromatography, is indicated in Table 1 below.
  • One of the additives according to the invention prepared in Example 1 is incorporated into a diesel fuel and the lubricating power of the fuel additive is measured according to the HFRR method described in standard ASTM 12156-1.
  • the diesel used in this example is a "biofree" B0 fuel and devoid of lubricant additive, containing less than 10 ppm / m of sulfur, the aromatic character of which is not very pronounced (22% m / m) and the density relatively low (821.9 g / L).
  • a single lubricant additive (DGMO, MGMO or TOFA) is incorporated, or a mixture of at least 2 lubricant additives including one of the DGMO additives according to the invention of Example 1 and at least one additive known lubricity (TOFA) and / or glycerol mono-oleate on the other hand.
  • the lubricating power of the product is measured according to the HFRR method described in ASTM 12156-1. AT.
  • the quantities indicated in table 4 are mass quantities (m / m) Table 4 Test No. AT B VS D E F G G G ' G " Fuel B7 B7 B7 B7 B7 B7 B7 B7 B7 Diesel detergent type PIBSA --- 330 ppm 330 ppm 330 ppm 170 ppm 170 ppm 330 ppm 330 then 170 ppm 170 ppm TOFA --- 200 ppm --- --- 200 ppm --- 200 ppm 200 then 0 ppm --- MGMO --- --- 200 ppm --- --- --- --- --- --- --- DGMO --- --- 200 ppm --- 200 ppm --- 0 then 200 ppm 200 ppm Type 1 deposit rating 8.7 -1 1.7 9.0 5.0 8.0 1.9 7.9 8.0 Listing of type 2 deposits 7.1 -1 6.3 7.9 2.8 7.2 2.5 6.4 5.6 Overall rating 8.2 -1 3.2 8.7 2.8 7.8 2.1 7.9

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EP13704128.1A 2012-02-17 2013-02-15 Additifs ameliorant la resistance a l'usure et au lacquering de carburants de type gazole ou biogazole Not-in-force EP2814917B1 (fr)

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US20160024411A1 (en) 2016-01-28
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